Oxidation of cysteine S-conjugates by rabbit liver microsomes and cDNA- expressed flavin-containing mono-oxygenases: Studies with S-(1,2- dichlorovinyl)-L-cysteine, S(1,2,2-trichlorovinyl)-L-cysteine, S-allyl-L- cysteine, and S-benzyl-L-cysteine

Molecular Pharmacology

Volumn 51, Issue 3, 1997, Pages 507-515

  Ripp, Sharon L ^a   Overby, Lila H ^b   Philpot, Richard M ^b   Elfarra, Adnan A ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b NATIONAL INSTITUTE OF ENVIRONMENTAL HEALTH SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 BENZYLIMIDAZOLE; ACETYLCYSTEINE; CYSTEINE CONJUGATE; CYSTEINE DERIVATIVE; CYTOCHROME P450 INHIBITOR; FLAVOPROTEIN; GLUTATHIONE; S (1,2 DICHLOROVINYL)CYSTEINE; S ALLYLCYSTEINE; SULFOXIDE; THIAMAZOLE; UNSPECIFIC MONOOXYGENASE;

ANIMAL TISSUE; ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CONTROLLED STUDY; ENZYME SUBSTRATE; LIVER MICROSOME; MALE; NONHUMAN; PRIORITY JOURNAL; RABBIT; SULFATION;

EID: 0030893969     PISSN: 0026895X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (32)

1. Monks, T. J., M. W. Anders, W. Dekant, J. L. Stevens, S. S. Lau, and P. J. Van Bladeren. Glutathione conjugate mediated toxicities. Toxicol. Appl. Pharmacol. 106:1-19 (1990).
2. Lock, E. A. Studies on the mechanism of nephrotoxicity and nephrocarcinogenicity of halogenated alkenes. CRC Crit. Rev. Toxicol. 19:23-42 (1988).
3. Kaye, C. M., J. J. Clapp, and L. Young. The metabolic formation of mercapturic acids from allyl halides. Xenobiotica 2:129-139 (1972).
4. Sklan, N. M., and E. A. Barnsley. The metabolism of S-methyl-L-cysteine. Biochem. J. 107:217-223 (1968).
5. Mitchell, S. C., R. L. Smith, R. H. Waring, and G. F. Aldington. The metabolism of S-methyl-L-cysteine in man. Xenobiotica 14:767-779 (1984).
6. Sausen, P. J., and A. A. Elfarra. Cysteine conjugate S-oxidase. J. Biol. Chem. 265:6139-6145 (1990).
7. Cashman, J. R. Structural and catalytic properties of the mammalian flavin-containing monooxygenase. Chem. Res. Toxicol. 8:165-181 (1995).
8. Lawton, M. P., J. R. Cashman, T. Cresteil, C. Dolphin, A. Elfarra, R. N. Hines, E. Hodgson, T. Kimura, J. Ozols, I. Phillips, R. M. Philpot, L. L. Poulsen, A. E. Rettie, D. E. Williams, and D. M. Ziegler. A nomenclature for the mammalian flavin-containing monooxygenase gene family based on amino acid sequence identities. Arch. Biochem. Biophys. 308:254-257 (1994).
9. Sausen, P. J., R. J. Duescher, and A. A. Elfarra. Further characterization and purification of the flavin-dependent S-benzyl-L-cysteine S-oxidase activities of rat liver and kidney microsomes. Mol. Pharmacol. 43:388-396 (1993).
10. Park, S. B., J. D. Osterloh, S. Vamvakas, M. Hashmi, M. W. Anders, and J. R. Cashman. Flavin-containing monooxygenase-dependent stereoselective s-oxygenation and cytotoxicity of cysteine s-conjugates and mercapturates. Chem. Res. Toxicol. 5:193-201 (1992).
11. Burnett, V. L., M. P. Lawton, and R. M. Philpot. Cloning and sequencing of flavin-containing monooxygenases FMO3 and FMO4 from rabbit and characterization of FMO3. J. Biol. Chem. 269:14314-14322 (1994).
12. Stoll, A., and E. Seebeck. Chemical investigations on alliin, the specific principle of garlic. Adv. Enzymol. Relat. Areas Mol. Biol. 11:377-400 (1951).
13. Ripp, S., R. Philpot, and A. Elfarra. Cysteine S-conjugate oxidation by flavin-containing monooxygenases. Fund. Appl. Toxicol. 30(Suppl.):214 (1996).
14. Sausen, P. J., and A. A. Elfarra. Reactivity of cysteine S-conjugate sulfoxides: formation of S-[1-chloro-2-(S-glutathionyl)vinyl]-L-cysteine sulfoxide by the reaction of S-(1,2-dichlorovinyl)-L-cysteine sulfoxide with glutathione. Chem. Res. Toxicol. 4:655-660 (1991).
15. McKinney, L. L., A. C. Eldridge, and J. C. Cowan. Cysteine thioethers from chloroethylenes. J. Am. Chem. Soc. 81:1423-1427 (1959).
16. Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:265-275 (1951).
17. Atta-Asafo-Adjei, E., M. P. Lawton, and R. M. Philpot. Cloning, sequencing, distribution, and expression in Escherichia coli of flavin-containing monooxygenase 1C1. J. Biol. Chem. 268:9681-9689 (1993).
18. Rettie, A. E., B. D. Bogucki, I. Lim, and G. P. Meier. Stereoselective sulfoxidation of a series of alkylp-tolyl sulfides by microsomal and purified flavin-containing monooxygenases. Mol. Pharmacol. 37:643-651 (1990).
19. Rettie, A. E., M. P. Lawton, A. J. M. Sadeque, G. P. Meier, and R. M. Philpot. Prochiral sulfoxidation as a probe for multiple forms of microsomal flavin-containing monooxygenase: studies with rabbit FMO1, FMO2, FMO3, and FMO5 expressed in Escherichia coli. Arch. Biochem. Biophys. 311:369-377 (1994).
20. Duescher, R. J., M. P. Lawton, R. M. Philpot, and A. A. Elfarra. Flavin-containing monooxygenase (FMO)-dependent metabolism of methionine and evidence for FMO3 being the major FMO involved in methionine sulfoxidation in rabbit liver and kidney microsomes. J. Biol. Chem. 269: 17525-17530 (1994).
21. Krause, R. J., S. L. Ripp, P. J. Sausen, L. H. Overby, R. M. Philpot, and A. A. Elfarra. Characterization of the methionine S-oxidase activity of rat liver and kidney microsomes: immunochemical and kinetic evidence for FMO3 being the major catalyst. Arch. Biochem. Biophys. 333:109-116 (1996).
22. Lash, L. H., P. J. Sausen, R. J. Duescher, J. A. Cooley, and A. A. Elfarra. Roles of cysteine conjugate β-lyase and S-oxidase in nephrotoxicity: studies with S-(1,2-dichlorovinyl)-L-cysteine and S-(1,2-dichlorovinyl)-L-cysteine sulfoxide. J. Pharmacol. Exp. Ther. 269:374-383 (1994).
23. Lomri, N., Z. Yang, and J. R. Cashman. Expression in Escherichia coli of the flavin-containing monooxygenase D (Form II) from adult human liver: determination of a distinct tertiary amine substrate specificity. Chem. Res. Toxicol. 6:425-429 (1993).
24. Lomri, N., Z. Yang, and J. R. Cashman. Regio-and stereoselective oxygenations by adult human liver flavin-containing monooxygenase 3. Comparison with forms 1 and 2. Chem. Res. Toxicol. 6:800-807 (1993).
25. Ziegler, D. M. Flavin-containing monooxygenases: catalytic mechanism and substrate specificities. Drug Metab. Rev. 19:1-32 (1988).
26. Werner, M., G. Birner, and W. Dekant. Sulfoxidation of mercapturic acids derived from tri-and tetrachlorothene by cytochromes P450 3A: a bioactivation reaction in addition to deacetylation and cysteine conjugate β-lyase mediated cleavage. Chem. Res. Toxicol. 9:41-49 (1996).
27. Welch, C., L. Wuarin, and N. Sidell. Antiproliferative effect of the garlic compound S-allyl cysteine on human neuroblastoma cells in vitro. Cancer Lett. 63:211-219 (1992).
28. Takeyama, H., D. S. B. Hoon, R. E. Saxton, D. L. Morton, and R. F. Irie. Growth inhibition and modulation of cell markers of melanoma by S-allyl cysteine. Oncology 50:63-69 (1993).
29. Sumiyoshi, H., and M. J. Wargovich. Chemoprevention of 1,2-dimethylhydrazine-induced colon cancer in mice by naturally occurring organosulfur compounds. Cancer Res. 50:5084-5087 (1990).
30. Hatono, S., A. Jimenez, and M. J. Wargovich. Chemopreventive effect of S-allyl cysteine and its relationship to the detoxification enzyme glutathione S-transferase. Carcinogenesis 17:1041-1044 (1996).
31. Green, T., and J. Odum. Structure/activity studies of the nephrotoxic and mutagenic action of cysteine conjugates of chloro-and fluoroalkenes. Chem.-Biol. Interact. 54:15-31 (1985).
32. Vamvakas, S., A. A. Elfarra, W. Dekant, D. Henschler, and M. W. Anders. Mutagenicity of amino acid and glutathione S-conjugates in the Ames test. Mutat. Res. 206:83-90 (1988).